메뉴 건너뛰기




Volumn 129, Issue 46, 2007, Pages 14112-14113

Enantioselective 1,4-addition reactions of diphenyl phosphite to nitroalkenes catalyzed by an axially chiral guanidine

Author keywords

[No Author keywords available]

Indexed keywords

GUANIDINE DERIVATIVE; NICKEL; NITROALKANE; PHOSPHITE;

EID: 36448993352     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0746619     Document Type: Article
Times cited : (126)

References (37)
  • 1
    • 0030922272 scopus 로고    scopus 로고
    • For reviews of the biological activity of α-amino phosphonic acids, see: a
    • For reviews of the biological activity of α-amino phosphonic acids, see: (a) Hiratake, J.; Oda, J. Biosci., Biotechnol., Biochem. 1997, 61, 211-218.
    • (1997) Biosci., Biotechnol., Biochem , vol.61 , pp. 211-218
    • Hiratake, J.1    Oda, J.2
  • 2
    • 0003563365 scopus 로고    scopus 로고
    • Kukhar, V. P, Hudson, H. R, Eds, John Wiley & Sons: New York
    • (b) Aminophosphonic and Aminophosphinic Acids; Kukhar, V. P.; Hudson, H. R., Eds.; John Wiley & Sons: New York, 2000.
    • (2000) Aminophosphonic and Aminophosphinic Acids
  • 3
    • 17244379375 scopus 로고    scopus 로고
    • For reviews of β-amino phosphonic acids, see: (a) Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899-931.
    • For reviews of β-amino phosphonic acids, see: (a) Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899-931.
  • 4
    • 84891299621 scopus 로고    scopus 로고
    • Palacios, F.; Alonso, C.; de los Santos, J. M. In Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E., Soloshonok, V. A., Eds.; Wiley: New York, 2005; pp 277-317.
    • (b) Palacios, F.; Alonso, C.; de los Santos, J. M. In Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E., Soloshonok, V. A., Eds.; Wiley: New York, 2005; pp 277-317.
  • 5
    • 33745390196 scopus 로고    scopus 로고
    • For a review of enantioselective synthesis of α-amino phosphonate derivatives, see
    • For a review of enantioselective synthesis of α-amino phosphonate derivatives, see: Ma, J.-A. Chem. Soc. Rev. 2006, 35, 630-636.
    • (2006) Chem. Soc. Rev , vol.35 , pp. 630-636
    • Ma, J.-A.1
  • 6
    • 6044269452 scopus 로고    scopus 로고
    • For general reviews of organocatalysts, see: a
    • For general reviews of organocatalysts, see: (a) Dalko, P. L.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 5138-5175
    • Dalko, P.L.1    Moisan, L.2
  • 9
    • 84868351603 scopus 로고    scopus 로고
    • For a review of 1,4-addition reaction of phosphorus nucleophiles with electron deficient alkenes, see
    • For a review of 1,4-addition reaction of phosphorus nucleophiles with electron deficient alkenes, see: Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur. J. Org. Chem. 2006, 29-49.
    • (2006) Eur. J. Org. Chem , pp. 29-49
    • Enders, D.1    Saint-Dizier, A.2    Lannou, M.-I.3    Lenzen, A.4
  • 10
    • 84982062886 scopus 로고    scopus 로고
    • Asymmetric 1,4-addition reactions of nitroalkenes with dialkyl phosphites. For chiral nitroalkenes, see: (a) Paulsen, H.; Greve, W. Chem. Ber. 1973, 103, 2114-2123.
    • Asymmetric 1,4-addition reactions of nitroalkenes with dialkyl phosphites. For chiral nitroalkenes, see: (a) Paulsen, H.; Greve, W. Chem. Ber. 1973, 103, 2114-2123.
  • 19
    • 33751402637 scopus 로고    scopus 로고
    • For 1,4-addition reaction of nitoalkenes with dialkyl phosphites catalyzed by achiral guanidine derivatives, see: d
    • For 1,4-addition reaction of nitoalkenes with dialkyl phosphites catalyzed by achiral guanidine derivatives, see: (d) Jiang, Z.; Zhang, Y.; Ye, W.; Tan, C.-H. Tetrahedron Lett. 2007, 45, 51-54.
    • (2007) Tetrahedron Lett , vol.45 , pp. 51-54
    • Jiang, Z.1    Zhang, Y.2    Ye, W.3    Tan, C.-H.4
  • 22
    • 15244362596 scopus 로고    scopus 로고
    • For enantioselective Mannich reaction catalyzed by chiral copper complexes, see: c
    • For enantioselective Mannich reaction catalyzed by chiral copper complexes, see: (c) Kjærsgaard, A.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 804-808.
    • (2005) Org. Biomol. Chem , vol.3 , pp. 804-808
    • Kjærsgaard, A.1    Jørgensen, K.A.2
  • 25
    • 0037006233 scopus 로고    scopus 로고
    • For a review of chiral guanidine catalysts, see: a
    • For a review of chiral guanidine catalysts, see: (a) Ishikawa, T.; Isobe, T. Chem. Eur. J. 2002, 8, 552-557.
    • (2002) Chem. Eur. J , vol.8 , pp. 552-557
    • Ishikawa, T.1    Isobe, T.2
  • 26
    • 0029990764 scopus 로고    scopus 로고
    • For selected examples of enantioselective catalysis by chiral guanidine derivatives, see: b
    • For selected examples of enantioselective catalysis by chiral guanidine derivatives, see: (b) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910-4911.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 4910-4911
    • Iyer, M.S.1    Gigstad, K.M.2    Namdev, N.D.3    Lipton, M.4
  • 33
    • 34547182502 scopus 로고    scopus 로고
    • Wang et al. reported that the 1,4-addition reaction of 2a with 3 catalyzed by quinine (10 mol % catalyst, in xylenes at -55 °C for 6 days) afforded the addition product (4a: R = Ph) in 82% yield with 70% ee. See: Wang, J.; Heikkinen, L. D.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Wang, W. Adv. Synth. Catal. 2007, 349, 1052-1056.
    • Wang et al. reported that the 1,4-addition reaction of 2a with 3 catalyzed by quinine (10 mol % catalyst, in xylenes at -55 °C for 6 days) afforded the addition product (4a: R = Ph) in 82% yield with 70% ee. See: Wang, J.; Heikkinen, L. D.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Wang, W. Adv. Synth. Catal. 2007, 349, 1052-1056.
  • 34
    • 33845220042 scopus 로고    scopus 로고
    • For a review of cinchona alkaloid derivatives as enantioselective organocatalysts, see
    • For a review of cinchona alkaloid derivatives as enantioselective organocatalysts, see: Marcelli, T.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 7496-7504.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 7496-7504
    • Marcelli, T.1    van Maarseveen, J.H.2    Hiemstra, H.3
  • 35
    • 0000905636 scopus 로고    scopus 로고
    • MS 4A was employed as an acid scavenger to avoid deactivation of the guanidine catalyst by acidic impurities which would be accidentally generated via partial hydrolysis of diphenyl phosphite (3). The reaction stopped in low conversion without MS 4A. For MS 4A as an acid scavenger, see: (a) Weinstock, L. M.; Karady, S.; Roberts, F. E.; Hoinowski, A. M.; Brenner, G. S.; Lee, T. B. K.; Lumma, W. C.; Sletzinger, M. Tetrahedron Lett. 1975, 46, 3979-3982.
    • MS 4A was employed as an acid scavenger to avoid deactivation of the guanidine catalyst by acidic impurities which would be accidentally generated via partial hydrolysis of diphenyl phosphite (3). The reaction stopped in low conversion without MS 4A. For MS 4A as an acid scavenger, see: (a) Weinstock, L. M.; Karady, S.; Roberts, F. E.; Hoinowski, A. M.; Brenner, G. S.; Lee, T. B. K.; Lumma, W. C.; Sletzinger, M. Tetrahedron Lett. 1975, 46, 3979-3982.
  • 37
    • 36448930695 scopus 로고    scopus 로고
    • 5 was hydrolyzed to N-Boc protected phosphonic acid without considerable loss of stereochemical integrity under hydrogenation conditions see Supporting Information for details, also see ref 11
    • 5 was hydrolyzed to N-Boc protected phosphonic acid without considerable loss of stereochemical integrity under hydrogenation conditions (see Supporting Information for details); also see ref 11.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.